May 26, 2025

Monday 5/26 Day 16. Witness Profile: Kid Cudi — From Man on the Moon to Diddy’s Courtroom Bombshell

Show Notes
Transcript

With court still closed, Did He Do It? dives into the life and legacy of kid Cuddy—hip-hop innovator, mental health advocate, and now a star witness in the Diddy trial. Host Nate Oliver traces Cuddy’s rise from Cleveland to global stardom, his battles with depression, and his explosive testimony about break-ins, firebombed cars, and Diddy’s chilling threats. Relive the courtroom drama and discover how Cuddy’s story of survival and truth is shaking the music world to its core.

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Calaruga Shark Media. Welcome back to Did He Do It?

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The Daily Podcast, bringing you every raw, unfiltered detail from

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the Sean Diddy Coombs sex trafficking and racketeering trial. I'm

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Nate Oliver, and with the court still closed for the

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holiday weekend, we're continuing our deep dive witness profiles. Today

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we turn the spotlight on a key figure whose testimony

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electrified the courtroom last week. Grammy winning rapper and actor

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Kid Cuddy. Scott Ramon Seguro Mescudy, known to the world

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as Kid Cuddy, was born January thirtieth, nineteen eighty four

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in Cleveland, Ohio. The youngest of four. Cuddy grew up

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in Shaker Heights, raised by his mother after losing his

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father to cancer at just eleven years old. That loss

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would shape him, fueling the intro respective, emotionally raw style

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that would later make him an icon for a generation

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of hip hop fans. Cuddy attended Shaker Heights High and

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briefly studied film at the University of Toledo before dropping

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out and heading to New York City in two thousand

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and five to chase his musical dreams. Cutty's breakthrough came

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in two thousand and eight when his mixtape A Kid

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Named Cuddy caught the ear of Kanye West. West signed

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him to Good Music, and Cutty's debut single, Day and

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Night became a global hit, peaking at number three on

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the Billboard Hot one hundred. His debut album, Man on

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the Moon The End of Day was released in two

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thousand and nine to critical acclaim, blending hip hop, rock,

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and electronic influences and tackling themes of depression, loneliness, and addiction.

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Cuddy's willingness to be vulnerable in his lyrics made him

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a cult hero, with tracks like Pursuit of Happiness and

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Soundtrack to My Life resonating with fans struggling with their

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own demons. Over the next decade, Kid Cuddy would become

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one of the most influential and innovative voices in hip hop.

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He collaborated with Kanye West, Jay Z, Travis Scott, and

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Eminem and formed the rock band Wizard. He's also built

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a career as an actor, appearing in HBO's How to

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Make It in America, the film Need for Speed, and

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the acclaimed indie James White. Cuddy has spoken publicly about

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his battles with mental health, checking himself into rehab in

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twenty sixteen and emerging as an advocate for therapy and

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self care. His openness about anxiety and depression has inspired

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a new generation of artists, including Travis Scott and lil

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Uzi Vert. But last week, Kid Cutty's name was on

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everyone's lips for a different reason. Called to the stand

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in the Diddy trial, Cutty delivered testimony that riveted the

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courtroom and sent shockwaves through the music world. We'll be

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back in a moment, Cutty told jurors about his brief

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romance with Cassie Ventura in twenty eleven, a relationship that

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he said quickly turned dangerous when Diddy found out. Cutty

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described getting a call from Cassie nervous and scared after

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Diddy discovered their relationship. That same day, Cutty learned Ditty

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had broken into his Hollywood Hills home. I called the police.

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I was worried for my safety and Cassie's, Cutty testified.

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He described a returning to find his Christmas presence unwrapped,

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his dog locked in the bathroom, and his security cameras repositioned. Cassie,

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he said, was very stressed, nervous, scared, didn't know what

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Sean Combs would do. Just weeks later, Cutty's Porsche was

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destroyed in a fire bombing. My dog's babysitter called and

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said my car was on fire, he told the court.

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The jury saw photos of the charred Porsche, a hole

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cut in the convertible roof and a Molotov cocktail found inside.

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It looked like the top of my Porsche was cut open,

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and that's where the Molotov cocktail was put in, Cutty said.

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He told the court he believed Didty was behind the arson,

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though Diddy denied it. When the two met an a

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tense confrontation at a Los Angeles hotel, Cutty described Ditty

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as standing by the window like a Marvel supervillain, calm

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and cold. When Cutty asked what would happen about the car?

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Did He replied, I don't know what you're talking about.

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Cutty said he left convinced Ditty was lying. Years later,

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at Soho House, did He unexpectedly apologized. Man, I just

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want to apologize for all that bullshit, Cutty told the jury.

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After the apology, I found peace with it. Cutty also

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testified that Cassie confided in him about Ditty's abuse. He

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would hit her sometimes kick her. Cutty said he broke

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up with Cassie because the drama was getting out of

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hand and he worried for both their safety. On cross examination,

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Ditty's lawyer tried to paint Cassie as living a double life,

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seeing both men at once. Cuddy admitted Cassie told him

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she and Ditty were broken up, but she was still

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seeing Ditty for freak off sex marathons. He said he

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didn't know the full extent of Cassie's relationship with Ditty

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at the time. For Kid Cuddy, the Ditty trial is

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just the latest twist in a career defined by reinvention, vulnerability,

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and survival from Cleveland to the top of the charts

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to the witness stand, and one of the most sensational

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trials in music history. Cuddy's story is a testament to

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resilience and a reminder that even hip hop's most fearless

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voices can find themselves caught in the crossfire of power, fame,

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and violence. That's our deep dive for today. When court resumes,

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will be right back with every new revelation, every legal

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twist and every rumor from inside and outside the courthouse.

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I'm Nate Oliver and this is did he do it?